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View PDF - Reluceo

Where’s the Puck Going to Be?
Opportunities for Renewable Biochemistry
Bio-based Chemicals: What, Why, How…
Olga Selifonova
Reluceo Holdings LLC
Agriculture and Rural
Executive Conference
Marshall, MN
March 11, 2014
All Sustainable Wealth of Civilization
is Derived from Agriculture and Forestry
2014 Reluceo Holdings LLC
2
FOOD
FEED
FUEL
FIBER
3
Major Opportunity for Underutilized
Non-Food Biomass
Renewable Chemicals
and Materials
4
Definitions
• Biomass - rapidly renewable organic matter
recently produced by modern living organisms
– as opposed to accumulated “fossil” organic matter over
geological periods lasting many millions of years (e.g. diagenesis
processes leading to the formation of petroleum and coal)
• Bio-based Chemicals – biochemicals produced
from sugars or its derivatives, fats, vegetable oils
and other biomass components via biological or
chemical conversions
• Conversion Technologies – fermentation,
biocatalysis, thermochemical conversions
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Aspirations for Industrial Bio-based Chemicals
• Planet and People friendly products
–
–
–
–
with exceptional performance
devoid of toxins
simple to make from renewable sources
beautifully designed to re-enter the carbon cycle when
they are no longer needed
– at competitive price
• Enable participation of Ag producers in
higher value applications for underutilized
non-food biomass
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Principal Sources of Biomass
• Plants
– Agricultural, Forestry, Algae
• Animals
– Livestock, marine organisms
• Microorganisms
– Fungi/yeast, bacteria, microalgae
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CO2
Sun light
C6
N, K, P …
H2O
Carbohydrates (C, H, O)
Sucrose (C6)
Starch (C6)
Cellulose (C6)
Hemicellulose (C5, C6)
Lignin
8
Feedstock complexity
• “Soft” Feedstocks
– Starch, Glucose, Sucrose
– Vegetable Oils, Fats
– Existing efficient crop processing technologies
• Dry and wet corn milling
• Beet or cane sugar extraction
• Vegetable oil extraction from oilseed…
• “Hard” Feedstocks
– Grassy/Woody Biomass
– Processing technologies for chemical separation are still
limited or under development
9
Evaluation of Biomass Sources
•
•
•
•
•
•
•
Chemistry
Price
Quantity
Consolidation
Seasonality
Sizing
Competing Uses
10
Representative Cellulosic Biomass Composition
• Carbohydrates (C6 and C5) are
the most abundant form of
organic carbon
– Lignin is the second most
C5, C6 abundant form of organic
C5, C6 carbon (a complex aromatic
Hemicellulose
cross-linked polymer)
20-35%
C6
C6
– Other classes of biomass
derived organic compounds
are proteins, fats, oils, DNA,
isoprenoids, etc. (limited
scalability for high volume
industrial uses)
11
Proven Conversion and Separation
Technologies for Cellulosic Biomass
• Pentosanes (C5) of hemicellulose are the easiest
to separate under mildest industrial conditions
– with a century of industrial practice
– furfural (for furfuryl alcohol)
– xylose (for xylitol)
• Cellulose (C6) is currently used in chiefly intact
form, with some chemical modifications
–
–
–
–
pulp and paper
soluble cellulose fibers
cellulose esters and ethers
fundamentals of the current state of cellulosic sugar technology (chemical,
enzymatic, pre-treatments) do not support cost-effective entry into
commodity chemicals or biofuels
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Bio-based Chemical Products
• Simple organic molecules
• Medium complexity compounds
(surfactants, “pre-polymers”, etc.)
• Large linear or branched/crosslinked
polymers/and co-polymers (plastics and
thermosets)
13
Age of Petroleum:
Fossil Carbon Use Peak
years
14
Bio-based Chemicals for Industrial Production
• “Drop-in” compounds: structures match exactly of those
produced industrially using temporarily available fossil carbon
sources (petroleum, gas, coal)
– Examples: ethanol, ethylene, polyethylene, ethylene glycol, vinyl acetate, polyvinyl
alcohol, 1,3-propanediol, 1,2-propylene glycol, butanol, acetone, isobutanol, acrylic acid,
propylene, isoprene, 1,4-butanediol
15
•
“Naturogenic” compounds: biochemical metabolites and their
derivatives with no practical or cost-effective routes available
using fossil carbon sources
– Fermentation-based examples: lactic acid and esters, citric acid, itaconic acid, gluconic
acid, lysine, glutamic acid
– Thermochemical process examples: sorbitol, xylitol, glycerol
16
•
“Naturogenic” compounds: biochemical metabolites and their
derivatives with no practical or cost-effective routes available
using fossil carbon sources
– Fermentation-based examples: lactic acid and esters, citric acid, itaconic acid, gluconic
acid, lysine, glutamic acid
– Thermochemical process examples: sorbitol, xylitol, glycerol.
• There are over 100 bio-based industrial chemical compounds
in production practice and at developmental stages
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Drop-in Example
Bio-Ethanol  Ethylene  Ethylene Glycol  PET
Plant-based PET bottles are recyclable,
but not degradable
18
Renewable Bio-based Chemicals:
Not a New Idea
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Millennia of Brewing to Alcohols
…from Booze to Fuel
http://www.germanbeerinstitute.com/history.html
http://www.minnpost.com
20
“Biotech” of the 19th Century
In 1893, Boehringer discovered that
lactic acid can be produced by bacteria
Albert Boehringer
(1861-1939)
1895 - The company pioneered
industrial scale production of
lactic acid for:
• dyeing
• leather
• textile
• food industry
http://www.boehringer-ingelheim.com/news/image_gallery/history.html
21
About 100 Years Later…
NatureWorks LLC
began in 1989 as a Cargill research project looking
for innovative uses of carbohydrates from plants as
feedstock for more sustainable plastics
http://www.natureworksllc.com/About-NatureWorks-LLC
2003 – world largest Lactic Acid
and PLA (polylactic acid polymer)
manufacturing
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The Early 20th Century
George Washington Carver
1941 - Henry Ford’s “Soybean Car”
1864-1943
Invented over 100 bio-based
products: plastics, paints, dyes, fuel
from agricultural feedstocks
(peanuts, soybeans, etc.)
https://www.thehenryford.org/research/soybeancar.aspx
Combining the auto industry with
agriculture
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Boom of Petrochemical Industry
Mid-Late 20th Century
McKinsey & Company
Availability of affordable
petroleum and globalization
suppressed development
of bio-based chemicals
and materials from
agricultural raw materials
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21th Century –
Time for Bio-Economy
25
26
27
A version of graphic representation of
“Top 12 DOE platform chemicals from glucose”
O
O
O
OH
HO
HO
OH
O
HO
OH
NH2
O
O
http://www.amazon.com/Top-Value-Added-ChemicalsBiomass/dp/1249193028/ref=sr_1_fkmr1_1?ie=UTF8&qid=1393721710
&sr=8-1fkmr1&keywords=Top+Value+Added+Chemicals+from+Biomass+Volum
e+I%E2%80%94Results+of+Screening+for+Potential+Candidates+from
+Sugars+and+Synthesis+Gas
HO
OH
O
HO
OH
O
OH OH
O
O
O
HO
HO
OH
NH2
O
OH
OH
O
O
O
HO
O
OH OH OH
O
OH
OH OH
OH
HO
OH OH OH
Produced by the Staff at
Pacific Northwest National Laboratory (PNNL)
National Renewable Energy Laboratory (NREL)
Office of Biomass Program (EERE)
For the Office of the Biomass Program
T. Werpy and G. Petersen, Editors, 2004
OH OH OH
OH OH O
The twelve sugar-based building blocks are 1,4-diacids
(succinic, fumaric and malic), 2,5-furan dicarboxylic acid, 3hydroxy propionic acid, aspartic acid, glucaric acid, glutamic
acid, itaconic acid, levulinic acid, 3-hydroxybutyrolactone,
glycerol, sorbitol, and xylitol/arabinitol.
http://www.osti.gov/scitech/biblio/926125
28
Our Green Chemistry Startups
2013
HOLDINGS LLC
2009
2009
XLTerra
2006
2002
29
Levulinic Ketals Technology Platform
2006
The first of the L-ketals discovered at Aromagen,
Ethyl Levulinate Glycerol Ketal has been
commercially introduced by Segetis.
O
HO
O
O
OR
As a key formulation ingredient, it can be found in
concentrated detergents and cleaning products
produced by Method and Seventh Generation.
30
XLTerra
High Performance Bioplastic from True
Biomass: Exceptional Value Proposition for
Conversion of Pentosanes (Hemicellulose)
C5 Chemical Platform
PXLK, Poly(Xylitan Levulinate Ketal), the
pinnacle of levulinic ketal platform chemistry,
is a colorless, ductile (not brittle), bioplastic
displaying:
Transparent Bioplastic
PXLK
…from Biomass
• exceptional optical clarity
• high impact resistance
• thermostability
• high heat deflection (Tg 115oC)
• excellent tensile strength
PXLK is superior to PLA and PHAs
O
O
O
O
O
O
n
PXLK can compete with best petroleumbased plastics.
31
Beyond Acrylics: Alternative
Superabsorbent Polymer (SAP)
C2 Chemical Platform
Based on Bio- Ethanol
Drought stress survival extended by 2 weeks in sand
No SAP
+0.1% PVGA
poly(vinyl alcohol)
Na, K PVGA*
OH OH OH
O
+
O
H
-H2O
O
OH
CO2(Na, K)
CO2H
glyoxylate
n
Novel Degradable PVGA SAP
based on industrial, degradable and
renewable polymer poly(vinyl alcohol)
acetalized with glyoxylic acid
(an ubiquitous natural product
produced commercially)
The PVGA SAP has exceptional
potential for water management and
water retention systems in precision
agriculture and re-vegetation, as well
as environmentally-responsible
personal hygiene products
(including baby diapers)
*representative
repeat unit
32
HOLDINGS LLC
Reluceo Holdings LLC has been formed and funded by Sergey
Selifonov and Olga Selifonova in December 2013 to continue building
our brand on intellectual and technology traditions for discovery and
pursuit of one-of-a-kind rule changing green chemistry processes and
renewable materials.
Formation of Reluceo Holdings LLC sets the scene for new projects,
opportunities and ventures.
33
Thank You
Contact: Olga Selifonova – olga_selifonova@reluceo.com
P.O. Box 47855, Plymouth, MN 55447, USA; Tel: +1-612-701-2280
34

View PDF - Reluceo

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